Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 1.SE, Problem 51AP
A carbanion is a species that contains a negatively charged, trivalent carbon.
(a) What is the electronic relationship between a carbanion and a trivalent nitrogen compound such as NH3?
(b) How many valence electrons does the negatively charged carbon atom have?
(c) What hybridization do you expect this carbon atom to have?
(d) What geometry is the carbanion likely to have?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Octocrylene is an ingredient found in topical sunscreens. It is a water-resistant molecule
that helps protect skin against harmful UVA and UVB radiation.
Octocrylene
Please answer the following questions:
(a) What is the hybridisation of each nonhydrogen atom?
(b) Are there two unique configurations possible about the C=C double bond? Please
explain your answer.
(c) Which of the two C-C bonds indicated by the arrows would you expect to be shorte.?
Please explain your answer.
The structure of caffeine is shown below.
(a) Complete the Lewis structure.
(b) How many pi bonds are present in caffeine? How many sigma bonds?
(c) Identify the hybridization of the carbon atoms.
(d) What is the value of the O-C-N angle?
The drawing below shows the overlap of two hybrid orbitalsto form a bond in a hydrocarbon. (a) Which of the followingtypes of bonds is being formed: (i) C¬C σ, (ii) C¬C π,or (iii) C¬H σ? (b) Which of the following could be theidentity of the hydrocarbon: (i) CH4, (ii) C2H6, (iii) C2H4, or(iv) C2H2?
Chapter 1 Solutions
Organic Chemistry
Ch. 1.3 - Give the ground-state electron configuration for...Ch. 1.3 - How many electrons does each of the following...Ch. 1.4 - Prob. 3PCh. 1.4 - Convert the following representation of ethane,...Ch. 1.4 - What are likely formulas for the following...Ch. 1.4 - Prob. 6PCh. 1.4 - Prob. 7PCh. 1.7 - Draw a line-bond structure for propane, CH3CH2CH3....Ch. 1.7 - Convert the following molecular model of hexane, a...Ch. 1.8 - Draw a line-bond structure for propene, CH3CH=CH2....
Ch. 1.8 - Draw a line-bond structure for 1, 3-butadiene,...Ch. 1.8 - Following is a molecular model of aspirin...Ch. 1.9 - Draw a line-bond structure for propyne, CH3C≡CH....Ch. 1.10 - Prob. 14PCh. 1.12 - Prob. 15PCh. 1.12 - Prob. 16PCh. 1.12 - The following molecular model is a representation...Ch. 1.SE - Convert each of the following molecular models...Ch. 1.SE - The following model is a representation of citric...Ch. 1.SE - The following model is a representation of...Ch. 1.SE - The following model is a representation of...Ch. 1.SE - How many valence electrons does each of the...Ch. 1.SE - Give the ground-state electron configuration for...Ch. 1.SE - Prob. 24APCh. 1.SE - Prob. 25APCh. 1.SE - Draw an electron-dot structure for acetonitrile,...Ch. 1.SE - Draw a line-bond structure for vinyl chloride,...Ch. 1.SE - Fill in any nonbonding valence electrons that are...Ch. 1.SE - Convert the following line-bond structures into...Ch. 1.SE - Convert the following molecular formulas into...Ch. 1.SE - Prob. 31APCh. 1.SE - Oxaloacetic acid, an important intermediate in...Ch. 1.SE - Prob. 33APCh. 1.SE - Potassium methoxide, KOCH3, contains both covalent...Ch. 1.SE - What is the hybridization of each carbon atom in...Ch. 1.SE - Prob. 36APCh. 1.SE - Prob. 37APCh. 1.SE - What bond angles do you expect for each of the...Ch. 1.SE - Propose structures for molecules that meet the...Ch. 1.SE - What kind of hybridization do you expect for each...Ch. 1.SE - Pyridoxal phosphate, a close relative of vitamin...Ch. 1.SE - Prob. 42APCh. 1.SE - Prob. 43APCh. 1.SE - Quetiapine, marketed as Seroquel, is a heavily...Ch. 1.SE - Tell the number of hydrogens bonded to each carbon...Ch. 1.SE - Why do you suppose no one has ever been able to...Ch. 1.SE - Allene, H2C=C=CH2, is somewhat unusual in that it...Ch. 1.SE - Allene (see Problem 1-47) is structurally related...Ch. 1.SE - Complete the electron-dot structure of caffeine,...Ch. 1.SE - Most stable organic species have tetravalent...Ch. 1.SE - A carbanion is a species that contains a...Ch. 1.SE - Divalent carbon species called carbenes are...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - Prob. 56APCh. 1.SE - Among the most common over-the-counter drugs you...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- In each of the following molecules, a central atom is surrounded by a total of three atoms or unshared electron pairs: SnCl2, BCl3, SO2. In which of these molecules would you expect the bond angle to be less than 120? Explain your reasoning.arrow_forwardButadiene, C4H6, is a planar molecule that has the followingcarbon–carbon bond lengths: (a) Predict the bond angles around each of the carbon atoms and sketch the molecule. (b) From left to right, what is the hybridization of each carbon atom in butadiene? (c) The middle C—C bond length in butadiene (1.48 Å) is a little shorter than the average C—C single bond length (1.54 Å). Does this imply that the middle C—C bond in butadiene is weaker or stronger than the average C—C single bond? (d) Based on your answer for part (c), discuss what additional aspects of bonding in butadiene might support the shorter middle C—C bond.arrow_forwardButadiene, C4H6, is a planar molecule that has the followingcarbon–carbon bond lengths:(a) Predict the bond angles around each of the carbon atomsand sketch the molecule. (b) From left to right, whatis the hybridization of each carbon atom in butadiene?(c) The middle C¬C bond length in butadiene (1.48 Å) isa little shorter than the average C¬C single bond length(1.54 Å). Does this imply that the middle C¬C bond in butadieneis weaker or stronger than the average C¬C singlebond? (d) Based on your answer for part (c), discuss what additional aspects of bonding in butadiene might supportthe shorter middle C¬C bond.arrow_forward
- Acetylsalicylic acid, better known as aspirin, has the Lewisstructure (a) What are the approximate values of the bond angles labeled1, 2, and 3? (b) What hybrid orbitals are used about thecentral atom of each of these angles? (c) How many s bondsare in the molecule?arrow_forwardDichloroethylene (C2H2Cl2) has three forms (isomers), eachof which is a different substance. (a) Draw Lewis structures ofthe three isomers, all of which have a carbon–carbon doublebond. (b) Which of these isomers has a zero dipole moment?(c) How many isomeric forms can chloroethylene, C2H3Cl,have? Would they be expected to have dipole moments?arrow_forward(a) What is the hybridization of chlorine in Clo4 ? (Type your answer using the format sp3 for sp3.) (b) What is the hybridization of bromine in BrF5? (c) What is the hybridization of bromine in BrO2 ?arrow_forward
- 2.arrow_forwardEthyl acetate, C4H8O2, is a fragrant substance used both as asolvent and as an aroma enhancer. Its Lewis structure is (a) What is the hybridization at each of the carbon atomsof the molecule? (b) What is the total number of valenceelectrons in ethyl acetate? (c) How many of the valence electronsare used to make s bonds in the molecule? (d) Howmany valence electrons are used to make p bonds? (e) Howmany valence electrons remain in nonbonding pairs in themolecule?arrow_forwardIf an electron is removed from a fluorine molecule, an F+2molecular ion forms.(a) Give the molecular electron configurations for F2 and F+2 (for the MOs constructed from valence AOs).(b) Give the bond order of each species.(c) Predict which species should be paramagnetic.(d) Predict which species has the greater bond dissociation energy.arrow_forward
- In following decomposition reaction:2C3H8(g)⟶ C2H4(g)+ C3H6(g) + CH4(g) + H2(g)For each of the four carbon compounds, do the following: (a) Draw Lewis structure.(b) Predict the geometry about the carbon atom.(c) Determine the hybridization of each type of carbon atom.arrow_forwardThe lactic acid molecule, CH3CH(OH)COOH, gives sourmilk its unpleasant, sour taste. (a) Draw the Lewis structurefor the molecule, assuming that carbon always forms fourbonds in its stable compounds. (b) How many π and howmany σ bonds are in the molecule? (c) Which CO bond isshortest in the molecule? (d) What is the hybridization ofatomic orbitals around the carbon atom associated withthat short bond? (e) What are the approximate bond anglesaround each carbon atom in the molecule?arrow_forward(e) What is the molecular structure of BrF5? (f) Give a VSEPR structure of BrFs. Label relevant angles. (g) Is BrFs polar or non-polar? (h) What is the hybridization of the central atom, Br?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningChemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
Stoichiometry - Chemistry for Massive Creatures: Crash Course Chemistry #6; Author: Crash Course;https://www.youtube.com/watch?v=UL1jmJaUkaQ;License: Standard YouTube License, CC-BY
Bonding (Ionic, Covalent & Metallic) - GCSE Chemistry; Author: Science Shorts;https://www.youtube.com/watch?v=p9MA6Od-zBA;License: Standard YouTube License, CC-BY
General Chemistry 1A. Lecture 12. Two Theories of Bonding.; Author: UCI Open;https://www.youtube.com/watch?v=dLTlL9Z1bh0;License: CC-BY